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Don’t be fooled by Tony Haile’s eclectic resume, which includes
stints in the Middle East, around-the-world yacht racing and
polar expeditions. “I see my career as being pretty consistent
even though for most people it probably looks bizarre,” says the
charismatic chief executive officer of media analytics company
Chartbeat. The common thread: “I want to
continuously find the things that challenge me and make me
better.”

Haile plunged headfirst into the world of startups in 2007 when a
friend asked him to take a look at a business plan for a social
network startup. Haile, a self-described “closet geek,” wrote a
six-page critique of what he considered a terrible business plan.
“They said ‘If you’re so smart why don’t you help run this
thing,’” says Haile, who, naturally, said yes.

In 2009, the New York startup studio Betaworks tapped him to help grow
Chartbeat from an in-house prototype to a viable business. The
now 55-employee firm builds tools for web publishers, from Al
Jazeera to The New York Times, that bring to light
data on where readers are clicking, why they stop reading and
how to adapt their content to keep them coming back.

Entrepreneur.com spoke with Haile about what keeps him
captivated.

ENTREPRENEUR: Beginning in 2000, you were part of crew
that finished an around the-world yacht race that covered 33,000
miles and lasted nearly a year. Did you grow up
sailing?Haile: I started out with little experience but
during university I got this idea that I wanted to do this. Every
summer I lived on a boat working as a crew, and I’d do boat
deliveries, Atlantic crossings, working for peanuts and learning
to sail big oceangoing boats. For the race, my position was
bowman, which meant I stood at the pointy end of the boat and got
the shit kicked out of me. At times it was utterly terrifying,
but I learned more about building a team and dealing with risk in
those 10 months than I have at any other point in my life.

ENTREPRENEUR: Companies charter boats for team-building
exercises, albeit around the harbor for a day. Do you think
sailing is a good analogy for leadership?Haile: I’ve been the guy serving drinks at those
events. Yacht racing is great for learning since there’s no one
leadership style. You have to apply different leadership styles
to different situations. There are times when everything is going
well, and you don’t need a heavy hand; people can have autonomy
and get the job done. Then there are times of crisis, when you’re
in a hurricane and the boat is in danger, where strong leadership
comes in.

ENTREPRENEUR: A couple of years after the race you moved
on to the North Pole. Are you prone to boredom?Haile: On the boat race someone gave me a
biography of [Sir Ernest] Shackleton [a famous
Antarctic explorer]. I came back and was looking for that next
test of myself. It’s not that I get bored. I get fascinated
with a topic and within that topic I get a chance to challenge
myself and learn where my boundaries are. Sometimes you come
across the boundaries very fast and sometimes you see beyond
the horizon.

Sailing taught me about teams and the polar world taught me about
individual effort and self-discipline. Apart from risk of losing
a limb, I find that startups are very similar. It’s not just what
you have to learn but what you have to unlearn. Everything that’s
true at five employees is very different with 25 people.

ENTREPRENEUR: Outside of work, how are you challenging
yourself these days?
Haile: I’ve been taking some Japanese. I wanted
something very different from my job and wanted to train my brain
in different ways. At first I thought it was incredibly logical,
and then I started finding out about the different quirks, all
the ways you can count to ten depending on the shape of the
object. I’m doing that and piano… I took it up a month ago. I
bought a keyboard, which my wife was horrified by because we have
a small apartment and it’s a rather large keyboard. Maybe one day
I can sing Billy Joel songs in Japanese.